Spark intimacy, trust, and understanding with these meaningful questions—perfect for date nights, road trips, or cozy evenings in.
Relationship therapist Esther Boykin says, “Regular, vulnerable conversations are the glue of lasting love.” Whether you’re newly dating or decades into marriage, these 85 questions will help you explore your partner’s heart, dreams, and values.
Pro Tip: Pair these with wine, dessert, or a walk! Start light, then dive deeper.
Family & Childhood
Who in your family are you most honest with?
What’s your favorite family tradition?
How did your family express love growing up?
Do you want kids? Why or why not?
What’s one thing you’d change about your upbringing?
Will you care for your parents as they age?
What childhood activity do you miss most?
What book shaped you as a kid?
What food tastes like “home” to you?
Which childhood rule would you keep (or ditch)?
Should kids do chores?
Which teacher changed your life?
How are you different from your high school self?
Who was your favorite Disney character?
Romance & Intimacy
What’s your love language?
Tell me about your first heartbreak.
Do you believe in twin flames?
When did you first say “I love you” (non-family)?
What does “good in bed” mean to you?
What ordinary action do you find sexy?
What touch says “I love you” to you?
Your Current Relationship
What’s your favorite memory of us?
What question are you afraid to ask me?
Name three things we have in common.
What’s one thing you’d change about us?
The Past
What’s your highest and lowest life moment?
Who deserves an apology from your past?
What’s your greatest accomplishment?
What’s your biggest mistake?
Describe a major health scare or injury.
When did you feel out of your comfort zone?
What risk would you take again?
Who do you miss from your past?
The Future
What would you ask a psychic about your future?
Describe your dream home.
Where do you see yourself in 5 years?
What’s your #1 goal in 10 years?
Where would you live if money didn’t matter?
Money & Values
Are you a spender or saver?
Should couples share bank accounts?
Splurge now or save for later?
What’s always worth the money?
What’s never worth splurging on?
What’s your biggest financial regret?
Travel the world or buy a dream home?
Personal Preferences
Plan your perfect solo day.
What’s your favorite alone-time activity?
What stresses you about traveling?
What’s your go-to self-care ritual?
Do you enjoy working out? How?
What cheers you up instantly?
How do you feel about recreational drugs?
When do you feel strongest?
When is lying okay (if ever)?
What movie have you rewatched most?
What obscure topic fascinates you?
Would you get a tattoo?
What popular thing do you dislike?
What quote would you frame on your wall?
Work & Career
Fame or wealth?
What motivates you at work?
What’s your dream job (no salary limits)?
Where’s your career in 10 years?
Who do you admire most at work?
Charity & Giving
Where would you donate $1 million?
What’s your recent act of kindness?
Have you donated to a stranger’s fundraiser?
Give time or money to a cause?
Philosophical
If you had one year to live, what would change?
How would you handle a terminal diagnosis?
Is forgiveness or acceptance more important?
Do you believe in a higher power?
What article changed your perspective?
Which sense would you sacrifice?
Self-Reflection
What are you secretly great at?
What do you wish people praised you for?
What are you most grateful for?
What are you selfish about?
What three words describe you?
What’s your biggest worry?
What skill do you want to improve?
When did you last work hard outside work/school?
Who’s your non-famous role model?
Who’d play you in a movie?
What’s your favorite way to recharge?
Final Tip: Save this list! Revisit it monthly to keep your connection fresh. As Boykin says, “Curiosity is the key to lifelong love.”
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